EP0126968B1 - Ergoline derivatives, processes for their preparation and pharmaceutical compositions containing same - Google Patents
Ergoline derivatives, processes for their preparation and pharmaceutical compositions containing same Download PDFInfo
- Publication number
- EP0126968B1 EP0126968B1 EP84104568A EP84104568A EP0126968B1 EP 0126968 B1 EP0126968 B1 EP 0126968B1 EP 84104568 A EP84104568 A EP 84104568A EP 84104568 A EP84104568 A EP 84104568A EP 0126968 B1 EP0126968 B1 EP 0126968B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- methyl
- ergoline
- dioxo
- group
- imidazolidinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
Definitions
- the invention relates to ergoline derivatives, to processes for their preparation and to pharmaceutical compositions containing them.
- EP-A-56 358 (2-haloergolinyl)-N',N'-diethylurea derivatives are disclosed, which show neuro- psychotropic and antihypertensive properties.
- the invention provides ergoline derivatives having the general formula I wherein
- halogen should be construed to preferably encompass chlorine and bromine atom; nevertheless, the term “halogen” also encompasses a fluorine atom.
- a hydrocarbon group having from 1 to 4 carbon atoms is intended to include alkyl, cycloalkyl and unsaturated (both ethylenically and acetylenically) groups.
- moieties include methyl, ethyl, n-propyl isopropyl, butyl, t-butyl, isobutyl, cyclopropyl, methylcyclopropyl, vinyl, allyl and propargyl.
- “Pharmaceutically acceptable salts” refers to those salts which retain the biological effectiveness and properties of the free bases and which are not biologically or otherwise undesiderable, formed with inorganic acids such as hydrochloric, hydrobromic, sulfuric, nitric or phosphoric acid; and organic acids such as acetic, propionic, glycolic, pyruvic, oxalic, malic, malonic, succinic, maleic, fumaric, tartaric, citric, benzoic, cinnamic, mandelic, methanesulfonic, ethanesulfonic, p-toluene sulfonic or salicylic acid.
- inorganic acids such as hydrochloric, hydrobromic, sulfuric, nitric or phosphoric acid
- organic acids such as acetic, propionic, glycolic, pyruvic, oxalic, malic, malonic, succinic, maleic, fumaric, tartaric, citric, be
- R 1 , R 2 , R 3 , R 7 , R 8 and R 5 are preferably hydrogen atoms.
- R 4 is a methyl group
- n is 1, B and R 9 are taken together and represent group.
- W and X are oxygen atoms
- A represents a group of formula -CH 2 - or ⁇ CH 2 ⁇ CH 2 ⁇ , most preferably A is a group of formula -CH 2 -.
- the present invention also provides a process for the preparation of a compound of formula I as described above which includes the step of condensing an ergoline derivative of the formula II wherein R 1 , R 2 , R 3 , R 4 , R 7 , R s , A, B and n are as above defined with a compound of formula III wherein R 5 and X are as above defined.
- the condensation process may be carried out in a solvent such as water, ethanol, acetic acid or pyridine with or without addition of acid, such as hydrogen chloride, at a temperature of from 50 to 100°C.
- a solvent such as water, ethanol, acetic acid or pyridine with or without addition of acid, such as hydrogen chloride, at a temperature of from 50 to 100°C.
- the crude product can be purified by crystallization or by chromatography.
- the ergoline derivatives of the general formula II, the starting materials for the process, are known compounds or can be prepared by established procedures starting from known compounds.
- the compounds of the general formula II wherein A represents a CH 2 ⁇ CHR 6 group can be obtained by reacting an appropriate ergoline primary amine with an acryl derivative of formula wherein R 6 and B are as above defined.
- a compound of formula wherein R 6 and B are as above defined and m is 0 or 1 can be made to react with an appropriate ergoline primary amine to give the compounds of the general formula II.
- the compounds of formula III, the other starting material for the process are known compounds and may be generated in situ by reaction of an appropriate salt thereof with an acid, such as hydrochloric acid.
- Free base forms of the compounds of formula I may be converted into acid addition salt forms in conventional manner and vice versa.
- the compounds according to the invention and their pharmaceutically acceptable salts exhibit pharmacological activities with the exception of those compounds, in which B is a cyano or carbamoyl group.
- the compounds are useful intermediates for forming the cyclic compounds, wherein R 9 and B taken together represent a group.
- prolactin secretion inhibition activity as indicated by an inhibition of the implatation of fertilized eggs in the uterus on day 5 after insemination of female rats [according to the principles of E Fluckiger et al., HANDB. EXP. PHARMAC., 49, 615, 1978].
- the compounds and the salts thereof of the present invention are active as antihypertensive agents.
- the animals were maintained in an environment of 36°C for 10-15 minutes to allow pulse pressure to be recorded and then systolic blood pressure and heart rate were measured by indirect tail cuff method using a W+W, BP Recorder, model 8005.
- the compounds were given orally, suspended in 5% arabic gum, once a day for 4 consecutive days and measurements were carried out before beginning the treatment and 1 and 5 hours after dosing, in both the first and fourth day of treatment.
- Drug doses refer to the free base. Controls animals received the vehicle only (0.2 ml/100 g b.w.).
- hydralazine (1-5 mg.Kg -1 p.o.) and a-methyldopa (30-100 mg.Kg- 1 p.o.) were also tested.
- Drug induced changes in systolic blood pressure and heart rate were calculated as differences from the pretreatment values and reported as means of 4 rats.
- Tables 1 and 2 show the results concerning the presently claimed compounds along with data concerning control vehicle and two reference standards, hydralazine and a-methyldopa.
- Systolic blood pressure (SBP) and heart rate (HR) remained stable throughout the duration of the experiment in vehicle treated rats; on the other hand, all our compounds were very active in reducing SBP in doses ranging from 1 to 20 mg.Kg-' p.o. This effect was not accompanied by a reflex increase in HR, whilst a moderate decrease in HR was instead observed with same of them.
- the invention further comprises a pharmaceutical composition containing a therapeutically effective amount of a compound of formula I or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.
- an effective dosage encompasses those amounts which yield the desired activity without causing adverse side effects.
- an effective dosage is in the range of about 0.001 to 0.5 mg/Kg day, preferably 0.01 to 0.25 mg/Kg day.
- the pharmaceutical carriers which are typically employed with the compounds of the invention may be solid or liquid and are generally selected dependent on the planned manner of administration.
- solid carriers include lactose, sucrose, gelatin and agar and the like
- liquid carriers include water, syrup, peanut oil and olive oil and the like.
- the combination of the selected compound and the carrier may be fashioned into numerous acceptable forms suchs such as tablets, capsules, suppositories, solutions, emulsion, powders and syrups.
- R 4 CH 3
- n 1
- X O
- R 5 CH 3
- Example 4 Operating as in Example 4, but employing 6-methyl-8 ⁇ -(N-ethoxycarbonylmethyl-aminomethyl)-ergoline (prepared as described in Example 3) instead of 6-methyl-8 ⁇ -[N-(2-methoxycarbonylethyl)-aminomethyl]-ergoline, the title compound, m.p. 165-167°C, was obtained.
- R 4 CH 3
- R 5 CH 2 CH 2 CH 3
- n 1
- A CH 2 CHR 6
- X O
- B COOCH 3 .
- R 4 CH 3
- R 5 CH 2 CH 2 CH 3
- n 1
- A CHR 6
- X O
- B COOCH 2 CH 3 .
- R 4 CH 3
- n 1
- A CHR 6
- R 5 CH 2 CH 2 CH 3 B
- Example 6 Operating as in Example 6, but employing isopropyl isocyanate instead of methyl isocyanate, the title compound, m.p. 118-120°C, was obtained.
- n 1
- A CH 2 CHR 6 , B and
- n 1
- A CHR 6 , B and
- R 4 n ⁇ C 3 H 7
- R 5 CH 3
- n 1
- A CH 2 CHR 6 , B and
- R 4 allyl
- R s CH 3
- n 1
- A CH 2 CHR 6 , B and
- R 4 n ⁇ C 3 H 7
- R 5 CH 3
- n 1
- A CHR 6 , B and
- R 4 allyl
- R 5 CH 3
- n 1
- A CHR 6 , B and
- R 2 SCH 3
- R 4 CH 3
- n 1
- A CHR 6 , B and
- R 4 CH 3
- R 7 and R 8 bond
- n 1
- A CH 2 CHR 6 , B and
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT84104568T ATE39352T1 (de) | 1983-04-28 | 1984-04-24 | Ergolinderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
MYPI88001619A MY104834A (en) | 1983-04-28 | 1988-12-31 | Ergoline deravatives, processes for their preparation and pharmaceutical compositions containing same. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8311679 | 1983-04-28 | ||
GB838311679A GB8311679D0 (en) | 1983-04-28 | 1983-04-28 | Ergoline derivatives |
GB838314816A GB8314816D0 (en) | 1983-05-27 | 1983-05-27 | Ergoline derivatives |
GB8314816 | 1983-05-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0126968A1 EP0126968A1 (en) | 1984-12-05 |
EP0126968B1 true EP0126968B1 (en) | 1988-12-21 |
Family
ID=26285978
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84104568A Expired EP0126968B1 (en) | 1983-04-28 | 1984-04-24 | Ergoline derivatives, processes for their preparation and pharmaceutical compositions containing same |
Country Status (18)
Country | Link |
---|---|
US (1) | US4690929A (ko) |
EP (1) | EP0126968B1 (ko) |
KR (1) | KR900008696B1 (ko) |
AU (1) | AU556968B2 (ko) |
CA (1) | CA1205801A (ko) |
DE (1) | DE3475709D1 (ko) |
DK (1) | DK162996C (ko) |
ES (1) | ES531906A0 (ko) |
FI (1) | FI81349C (ko) |
GR (1) | GR79575B (ko) |
HU (1) | HU198713B (ko) |
IE (1) | IE57240B1 (ko) |
IL (1) | IL71633A (ko) |
NO (1) | NO161562C (ko) |
PH (1) | PH21123A (ko) |
PT (1) | PT78496B (ko) |
SU (1) | SU1327788A3 (ko) |
YU (1) | YU43357B (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8952128B2 (en) | 2012-11-01 | 2015-02-10 | Ipsen Pharma S.A.S. | Somatostatin-dopamine chimeric analogs |
US9777039B2 (en) | 2012-11-01 | 2017-10-03 | Ipsen Pharma S.A.S. | Somatostatin analogs and dimers thereof |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8714767D0 (en) * | 1987-06-24 | 1987-07-29 | Erba Farmitalia | Egoline derivatives |
HU196399B (en) * | 1983-02-16 | 1988-11-28 | Sandoz Ag | Process for producing ergoline derivatives and pharmaceutical compositions comprising such compounds |
GB8501078D0 (en) * | 1985-01-16 | 1985-02-20 | Erba Farmitalia | Piperazin-1-yl-ergo-line derivatives |
GB2173189B (en) * | 1985-02-21 | 1988-04-27 | Maruko Pharmaceutical Co | Ergoline derivatives and salts thereof and pharmaceutical compositions thereof |
GB8515528D0 (en) * | 1985-06-19 | 1985-07-24 | Erba Farmitalia | Ergoline derivatives |
US4801712A (en) * | 1985-06-24 | 1989-01-31 | Eli Lilly And Company | 2-Alkyl(or phenyl)thio-6-n-alkylergolines are dopamine D-1 antagonists without D-2 agonist activity |
DE3528576A1 (de) * | 1985-08-06 | 1987-02-19 | Schering Ag | Verfahren zur herstellung von ergolin-thioharnstoffen |
DE3535929A1 (de) * | 1985-10-04 | 1987-04-09 | Schering Ag | 1,2-disubstituierte ergolinderivate |
GB8617907D0 (en) * | 1986-07-22 | 1986-08-28 | Erba Farmitalia | Tetracyclic indole derivatives |
GB8702364D0 (en) * | 1987-02-03 | 1987-03-11 | Erba Farmitalia | Ergolinyl heterocycles |
DK338789A (da) * | 1988-07-15 | 1990-01-16 | Schering Ag | 2-substituerede ergolinylurinstofderivater og fremgangsmaade til fremstilling deraf, deres anvendelse som laegemidler samt mellemprodukter til fremstilling deraf |
CA2049053A1 (en) * | 1990-01-25 | 1991-07-26 | Sergio Mantegani | Process for preparing ergoline derivatives |
GB9006772D0 (en) * | 1990-03-27 | 1990-05-23 | Erba Carlo Spa | 4-piperidinyl-ergoline derivatives |
DE69330601T2 (de) * | 1992-12-24 | 2002-07-04 | Pharmacia & Upjohn Spa | Serotoninergische ergolin derivate |
ES2325880T3 (es) | 2001-06-08 | 2009-09-23 | Ipsen Pharma | Analogos quimericos de somatostatina-dopamina. |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE622316A (ko) * | 1961-09-11 | |||
SE393615B (sv) * | 1971-05-19 | 1977-05-16 | Sandoz Ag | Forfarande for framstellning av 6-metyl-8 beta-ureidometyl-ergolener |
NL7416120A (nl) * | 1973-12-21 | 1975-06-24 | Farmaceutici Italia | Werkwijze voor het bereiden van pyrimidinoami- nomethylergolinederivaten. |
US3996228A (en) * | 1973-12-21 | 1976-12-07 | Societa' Farmaceutici Italia S.P.A. | Pyrimidinoaminoethyl ergoline derivatives |
DE2456930A1 (de) * | 1974-12-02 | 1976-08-12 | Tesch Kg E | Elektronisches zeitspeicherrelais |
CH615181A5 (en) * | 1975-05-21 | 1980-01-15 | Sandoz Ag | Process for the preparation of novel ergolene derivatives |
GB2056437A (en) * | 1979-08-07 | 1981-03-18 | Erba Farmitalia | Secoergoline derivatives |
DE3001752A1 (de) * | 1980-01-16 | 1981-07-30 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Verfahren zur herstellung von 8(alpha)-substituierten 6-methylergolinen |
DD154897A1 (de) * | 1980-12-02 | 1982-04-28 | Seifert Karlheinz Dipl Chem Dr | Verfahren zur herstellung von 8-substituierten ergolinen |
DE3101535A1 (de) * | 1981-01-14 | 1982-08-12 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue (2-halogen-ergolinyl)-n'.n'-diethyl-harnstoffderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel |
GB2112382B (en) * | 1981-11-06 | 1985-03-06 | Erba Farmitalia | Ergoline derivatives |
-
1984
- 1984-04-23 PH PH30590A patent/PH21123A/en unknown
- 1984-04-24 SU SU843728545A patent/SU1327788A3/ru active
- 1984-04-24 EP EP84104568A patent/EP0126968B1/en not_active Expired
- 1984-04-24 DE DE8484104568T patent/DE3475709D1/de not_active Expired
- 1984-04-24 CA CA000452664A patent/CA1205801A/en not_active Expired
- 1984-04-25 IL IL71633A patent/IL71633A/xx not_active IP Right Cessation
- 1984-04-25 FI FI841631A patent/FI81349C/fi not_active IP Right Cessation
- 1984-04-25 ES ES531906A patent/ES531906A0/es active Granted
- 1984-04-26 US US06/604,041 patent/US4690929A/en not_active Expired - Fee Related
- 1984-04-26 GR GR74511A patent/GR79575B/el unknown
- 1984-04-26 IE IE1018/84A patent/IE57240B1/en not_active IP Right Cessation
- 1984-04-26 PT PT78496A patent/PT78496B/pt not_active IP Right Cessation
- 1984-04-26 YU YU742/84A patent/YU43357B/xx unknown
- 1984-04-26 NO NO841657A patent/NO161562C/no unknown
- 1984-04-27 KR KR1019840002271A patent/KR900008696B1/ko not_active IP Right Cessation
- 1984-04-27 HU HU841656A patent/HU198713B/hu not_active IP Right Cessation
- 1984-04-27 DK DK212784A patent/DK162996C/da not_active IP Right Cessation
- 1984-04-27 AU AU27421/84A patent/AU556968B2/en not_active Ceased
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8952128B2 (en) | 2012-11-01 | 2015-02-10 | Ipsen Pharma S.A.S. | Somatostatin-dopamine chimeric analogs |
US9603942B2 (en) | 2012-11-01 | 2017-03-28 | Ipsen Pharma S.A.S. | Somatostatin-dopamine chimeric analogs |
US9731027B2 (en) | 2012-11-01 | 2017-08-15 | Ipsen Pharma S.A.S. | Somatostatin-dopamine chimeric analogs |
US9777039B2 (en) | 2012-11-01 | 2017-10-03 | Ipsen Pharma S.A.S. | Somatostatin analogs and dimers thereof |
Also Published As
Publication number | Publication date |
---|---|
DK162996C (da) | 1992-06-01 |
DK212784A (da) | 1984-10-29 |
CA1205801A (en) | 1986-06-10 |
IE57240B1 (en) | 1992-06-17 |
PH21123A (en) | 1987-07-27 |
YU74284A (en) | 1986-10-31 |
IL71633A (en) | 1987-12-20 |
KR900008696B1 (ko) | 1990-11-27 |
EP0126968A1 (en) | 1984-12-05 |
IL71633A0 (en) | 1984-07-31 |
SU1327788A3 (ru) | 1987-07-30 |
FI81349B (fi) | 1990-06-29 |
ES8506031A1 (es) | 1985-06-01 |
KR840008353A (ko) | 1984-12-14 |
HUT34024A (en) | 1985-01-28 |
NO841657L (no) | 1984-10-29 |
AU2742184A (en) | 1984-11-01 |
NO161562C (no) | 1989-08-30 |
NO161562B (no) | 1989-05-22 |
HU198713B (en) | 1989-11-28 |
FI841631A0 (ko) | 1984-04-25 |
GR79575B (ko) | 1984-10-30 |
AU556968B2 (en) | 1986-11-27 |
YU43357B (en) | 1989-06-30 |
DE3475709D1 (en) | 1989-01-26 |
FI81349C (fi) | 1990-10-10 |
FI841631A (ko) | 1984-10-29 |
DK162996B (da) | 1992-01-06 |
PT78496B (en) | 1986-07-22 |
ES531906A0 (es) | 1985-06-01 |
US4690929A (en) | 1987-09-01 |
PT78496A (en) | 1984-05-01 |
DK212784D0 (da) | 1984-04-27 |
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